Compounds on the basis of 2- and 4-chromenylidene-merocyanines respectively, and their use

Abstract

The invention relates to compounds based on merocyanines with the general formulas I and/or II, where n=0 or an integer from 1 to 3, X=O or S and the residues R 1 to R 12 are the same or different and signify in particular hydrogen or various organic residues, without or with functional groups, and R 2 incorporates an amine function. The compounds in accordance with the invention are suitable as fluorescent dyes (fluorophores) for used in optical determination and demonstration methods, in particular those employing fluorescence, for example in medicine, pharmacology and the biological, materials and environmental sciences. They are characterized by high photostability and long storage life, and exhibit a high fluorescence quantum yield. Excitation causing them to emit light can be achieved in a simple manner, by white-light sources or by laser irradiation in the UV, visible or NIR spectral region.

1. A compound of the formula I or II 
       
         
           
           
               
               
           
         
       
       wherein
 (a) R 1  and R 3  to R 12  may each be the same or different and is selected from the group consisting of hydrogen, chlorine, bromine, and a substituent selected from the group consisting of an alkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, alkyloxy, alkylmercapto, aryloxy, arylmercapto, heteroaryloxy, heretoarylmercapto, cyano, an isocyano, isothiocyano, hydrazino, amino, monochloro- and dichloro- or monobromo- and dibromo-triazinyl, aziridino, sulfonyl halogenid, N-hydroxysuccinyl, imido, glyoxyl, maleimido, iodacetamido, and phosphoramido; and wherein the substituent may also contain, apart from carbon and hydrogen, as many as 4 oxygen atoms and 0, 1 or 2 nitrogen atoms, or one sulfur atom, or one sulfur and one nitrogen atom; 
 (b) R 1  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , and R 6  and R 7  together may form an aromatic, non-aromatic or nitrogen-containing 5- or 6-member ring; 
 (c) X represents oxygen or sulfur; 
 (d) n is zero, 1, 2 or 3; 
 (e) and with the proviso that R 2  must contain a nitrogen atom and is a substituted or unsubstituted amino group or a nitrogen-containing 5- or 6- membered ring. 
 
     
     
       2. A compound as claimed in  claim 1  wherein each of the residues R 1  and R 3  to R 12  have at most 10 carbon atoms. 
     
     
       3. A compound as claimed in  claim 1  wherein not more than four of the residues R 1  and R 3  to R 12  contain a sulfur atom. 
     
     
       4. A compound as claimed in  claim 1  wherein said groups R 1  and R 3  to R 12  contain from 1 to 6 carbon atoms. 
     
     
       5. A compound as claimed in  claim 1 , wherein X represents oxygen. 
     
     
       6. A compound as claimed in  claim 1 , wherein n represents zero, 1 or 2.